TWI479008B - 穩定且有效之電致發光材料 - Google Patents
穩定且有效之電致發光材料 Download PDFInfo
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- TWI479008B TWI479008B TW102114261A TW102114261A TWI479008B TW I479008 B TWI479008 B TW I479008B TW 102114261 A TW102114261 A TW 102114261A TW 102114261 A TW102114261 A TW 102114261A TW I479008 B TWI479008 B TW I479008B
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- alkyl
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- 239000000463 material Substances 0.000 title description 203
- 150000001875 compounds Chemical class 0.000 claims description 102
- 239000003446 ligand Substances 0.000 claims description 85
- 229910052751 metal Inorganic materials 0.000 claims description 67
- 239000002184 metal Substances 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000010410 layer Substances 0.000 description 171
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 88
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 239000007983 Tris buffer Substances 0.000 description 67
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
- 239000011541 reaction mixture Substances 0.000 description 49
- 238000010992 reflux Methods 0.000 description 48
- 239000000047 product Substances 0.000 description 43
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 37
- 239000000203 mixture Substances 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 34
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 33
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 29
- 238000003756 stirring Methods 0.000 description 28
- 239000000758 substrate Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- 230000032258 transport Effects 0.000 description 24
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 230000005525 hole transport Effects 0.000 description 21
- 239000007788 liquid Substances 0.000 description 21
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 20
- 230000008020 evaporation Effects 0.000 description 20
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 19
- UGPGOSOMRCGTQE-UHFFFAOYSA-K [Al+3].CC1=NC2=C(C=CC=C2C=C1C=1C(=C(C=CC1C1=CC=CC=C1)[O-])C=1C(=NC2=C(C=CC=C2C1)O)C)O.CC1=NC2=C(C=CC=C2C=C1C=1C(=C(C=CC1C1=CC=CC=C1)[O-])C=1C(=NC2=C(C=CC=C2C1)O)C)O.CC1=NC2=C(C=CC=C2C=C1C=1C(=C(C=CC1C1=CC=CC=C1)[O-])C=1C(=NC2=C(C=CC=C2C1)O)C)O Chemical compound [Al+3].CC1=NC2=C(C=CC=C2C=C1C=1C(=C(C=CC1C1=CC=CC=C1)[O-])C=1C(=NC2=C(C=CC=C2C1)O)C)O.CC1=NC2=C(C=CC=C2C=C1C=1C(=C(C=CC1C1=CC=CC=C1)[O-])C=1C(=NC2=C(C=CC=C2C1)O)C)O.CC1=NC2=C(C=CC=C2C=C1C=1C(=C(C=CC1C1=CC=CC=C1)[O-])C=1C(=NC2=C(C=CC=C2C1)O)C)O UGPGOSOMRCGTQE-UHFFFAOYSA-K 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- 150000003384 small molecules Chemical class 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 238000003828 vacuum filtration Methods 0.000 description 19
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 18
- 229910052707 ruthenium Inorganic materials 0.000 description 18
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 17
- 239000002019 doping agent Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 229910052741 iridium Inorganic materials 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 238000006467 substitution reaction Methods 0.000 description 14
- IWUVCNQOYRJIAB-UHFFFAOYSA-N 2-(3-bromophenyl)-5-methylpyridine Chemical compound N1=CC(C)=CC=C1C1=CC=CC(Br)=C1 IWUVCNQOYRJIAB-UHFFFAOYSA-N 0.000 description 13
- -1 fluorine-substituted benzene ring Chemical group 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000539 dimer Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 239000011368 organic material Substances 0.000 description 12
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000011241 protective layer Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 230000004888 barrier function Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 238000000151 deposition Methods 0.000 description 10
- 238000001194 electroluminescence spectrum Methods 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 238000005292 vacuum distillation Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000006069 Suzuki reaction reaction Methods 0.000 description 8
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- 125000005647 linker group Chemical group 0.000 description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 8
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 8
- AGQLSVGMHSEHRH-UHFFFAOYSA-N 2-[3-(2-methylphenyl)phenyl]pyridine Chemical compound CC1=CC=CC=C1C1=CC=CC(C=2N=CC=CC=2)=C1 AGQLSVGMHSEHRH-UHFFFAOYSA-N 0.000 description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 7
- 101001003146 Mus musculus Interleukin-11 receptor subunit alpha-1 Proteins 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 150000004696 coordination complex Chemical class 0.000 description 7
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 230000000670 limiting effect Effects 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical compound CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 6
- 229940093475 2-ethoxyethanol Drugs 0.000 description 6
- MCIPELGMHYHVBA-UHFFFAOYSA-N 3,4-dimethyl-2-phenylpyridine Chemical compound CC1=CC=NC(C=2C=CC=CC=2)=C1C MCIPELGMHYHVBA-UHFFFAOYSA-N 0.000 description 6
- LMGVDGBKURRIHA-UHFFFAOYSA-N 4,5-dimethyl-2-phenylpyridine Chemical compound C1=C(C)C(C)=CN=C1C1=CC=CC=C1 LMGVDGBKURRIHA-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QWUJMRNKWKTFKN-UHFFFAOYSA-N CCOC(C(C)CCC1)=C1NN Chemical compound CCOC(C(C)CCC1)=C1NN QWUJMRNKWKTFKN-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000002800 charge carrier Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000000412 dendrimer Substances 0.000 description 6
- 229920000736 dendritic polymer Polymers 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 125000002524 organometallic group Chemical group 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 229910052703 rhodium Inorganic materials 0.000 description 5
- 238000002207 thermal evaporation Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- AFSSVCNPDKKSRR-UHFFFAOYSA-N (3-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Br)=C1 AFSSVCNPDKKSRR-UHFFFAOYSA-N 0.000 description 4
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 4
- WLPFTJXVEBANAM-UHFFFAOYSA-N 2-(3-bromophenyl)pyridine Chemical compound BrC1=CC=CC(C=2N=CC=CC=2)=C1 WLPFTJXVEBANAM-UHFFFAOYSA-N 0.000 description 4
- KJNZQKYSNAQLEO-UHFFFAOYSA-N 2-(4-methylphenyl)pyridine Chemical compound C1=CC(C)=CC=C1C1=CC=CC=N1 KJNZQKYSNAQLEO-UHFFFAOYSA-N 0.000 description 4
- OTHVRXCVMLINFQ-UHFFFAOYSA-N 2-[3-(3-fluorophenyl)phenyl]pyridine Chemical compound FC1=CC=CC(C=2C=C(C=CC=2)C=2N=CC=CC=2)=C1 OTHVRXCVMLINFQ-UHFFFAOYSA-N 0.000 description 4
- GREMYQDDZRJQEG-UHFFFAOYSA-N 2-methyl-6-phenylpyridine Chemical compound CC1=CC=CC(C=2C=CC=CC=2)=N1 GREMYQDDZRJQEG-UHFFFAOYSA-N 0.000 description 4
- RYRDKQYQAMRCHF-UHFFFAOYSA-N 3-methyl-2-(4-methylphenyl)pyridine Chemical compound C1=CC(C)=CC=C1C1=NC=CC=C1C RYRDKQYQAMRCHF-UHFFFAOYSA-N 0.000 description 4
- FXKYLAPEKMFPOD-UHFFFAOYSA-N 4-methyl-1-phenylisoquinoline Chemical compound C12=CC=CC=C2C(C)=CN=C1C1=CC=CC=C1 FXKYLAPEKMFPOD-UHFFFAOYSA-N 0.000 description 4
- RQPPYGJFZXBYKW-UHFFFAOYSA-N 4-methyl-2-(3-phenylphenyl)pyridine Chemical compound CC1=CC=NC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 RQPPYGJFZXBYKW-UHFFFAOYSA-N 0.000 description 4
- WUXLUKWFQALJDH-UHFFFAOYSA-N 5-methyl-2-(3-phenylphenyl)pyridine Chemical compound N1=CC(C)=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 WUXLUKWFQALJDH-UHFFFAOYSA-N 0.000 description 4
- FQUOLAWBNANVNG-UHFFFAOYSA-N 5-tert-butyl-2-(3-phenylphenyl)pyridine Chemical compound N1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 FQUOLAWBNANVNG-UHFFFAOYSA-N 0.000 description 4
- RBTDEZRSPONUEY-UHFFFAOYSA-N CC1=C(C=C2C=CC=C(C2=N1)O)C3=C(C=CC(=C3C4=C(N=C5C(=C4)C=CC=C5O)C)O)C6=CC=CC=C6 Chemical compound CC1=C(C=C2C=CC=C(C2=N1)O)C3=C(C=CC(=C3C4=C(N=C5C(=C4)C=CC=C5O)C)O)C6=CC=CC=C6 RBTDEZRSPONUEY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- LDRHTDGHYORUMG-UHFFFAOYSA-N 2-(4-bromophenyl)-5-methylpyridine Chemical compound N1=CC(C)=CC=C1C1=CC=C(Br)C=C1 LDRHTDGHYORUMG-UHFFFAOYSA-N 0.000 description 3
- JOACEYFXFYWUIK-UHFFFAOYSA-N 2-bromo-4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC(Br)=C1 JOACEYFXFYWUIK-UHFFFAOYSA-N 0.000 description 3
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 3
- VKRKOOOBSIIARV-UHFFFAOYSA-N 2-methylidene-3,4-dihydronaphthalen-1-one Chemical compound C1=CC=C2C(=O)C(=C)CCC2=C1 VKRKOOOBSIIARV-UHFFFAOYSA-N 0.000 description 3
- IIYNXXPDUFXMIA-UHFFFAOYSA-N 3,4,5-trimethyl-2-phenylpyridine Chemical compound CC1=C(C)C(C)=CN=C1C1=CC=CC=C1 IIYNXXPDUFXMIA-UHFFFAOYSA-N 0.000 description 3
- IEUZDMOVRGODGO-UHFFFAOYSA-N 4-methyl-1-phenyl-3,4-dihydroisoquinoline Chemical compound C12=CC=CC=C2C(C)CN=C1C1=CC=CC=C1 IEUZDMOVRGODGO-UHFFFAOYSA-N 0.000 description 3
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- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
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- 150000003852 triazoles Chemical class 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/006—Palladium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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Applications Claiming Priority (3)
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|---|---|---|---|
| US10/886,367 US20060008671A1 (en) | 2004-07-07 | 2004-07-07 | Electroluminescent efficiency |
| US11/018,453 US7709100B2 (en) | 2004-07-07 | 2004-12-21 | Electroluminescent efficiency |
| US68269005P | 2005-05-19 | 2005-05-19 |
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| TW201333161A TW201333161A (zh) | 2013-08-16 |
| TWI479008B true TWI479008B (zh) | 2015-04-01 |
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| TW094123051A TWI399421B (zh) | 2004-07-07 | 2005-07-07 | 穩定且有效之電致發光材料 |
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| KR (2) | KR101214539B1 (ko) |
| TW (2) | TWI479008B (ko) |
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- 2005-07-07 WO PCT/US2005/024295 patent/WO2006014599A2/en active Application Filing
- 2005-07-07 EP EP20217507.1A patent/EP3855519A3/en active Pending
- 2005-07-07 EP EP05770339.9A patent/EP1763902B1/en active Active
- 2005-07-07 TW TW102114261A patent/TWI479008B/zh active
- 2005-07-07 TW TW094123051A patent/TWI399421B/zh active
- 2005-07-07 JP JP2007520546A patent/JP5009154B2/ja active Active
- 2005-07-07 KR KR1020127018882A patent/KR101258042B1/ko active IP Right Grant
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| WO2004026886A2 (de) * | 2002-08-24 | 2004-04-01 | Covion Organic Semiconductors Gmbh | Rhodium-und iridium-komplexe |
| TWI399421B (zh) * | 2004-07-07 | 2013-06-21 | Universal Display Corp | 穩定且有效之電致發光材料 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200621935A (en) | 2006-07-01 |
| EP1763902A2 (en) | 2007-03-21 |
| KR20120089376A (ko) | 2012-08-09 |
| JP5577370B2 (ja) | 2014-08-20 |
| EP3428986B1 (en) | 2021-01-20 |
| JP5009154B2 (ja) | 2012-08-22 |
| EP3855519A3 (en) | 2021-09-22 |
| JP2008505925A (ja) | 2008-02-28 |
| EP3428986A1 (en) | 2019-01-16 |
| KR101258042B1 (ko) | 2013-04-24 |
| KR101214539B1 (ko) | 2012-12-24 |
| EP3855519A2 (en) | 2021-07-28 |
| WO2006014599A2 (en) | 2006-02-09 |
| EP1763902B1 (en) | 2018-08-29 |
| JP2012149083A (ja) | 2012-08-09 |
| TWI399421B (zh) | 2013-06-21 |
| TW201333161A (zh) | 2013-08-16 |
| WO2006014599A3 (en) | 2006-06-22 |
| KR20070050438A (ko) | 2007-05-15 |
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